Middlesboro Vacations

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Find the Best Middlesboro Vacation Packages

Middlesboro Hotel Deals

Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is NT$3,163 per night from Jul 13 to Jul 14
NT$3,163
NT$3,487 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (736 reviews)
"Very clean and quiet place to stay. The breakfast was really good also. This stay exceeded my expectations. I would recommend this for either business or pleasure trips."

Reviewed on 2025/6/22

Sleep Inn & Suites
Holiday Inn Express Middlesboro by IHG
Holiday Inn Express Middlesboro by IHG
2.5 out of 5
1252 N 12th St, Middlesboro, KY
Fully refundable
The price is NT$3,721 per night from Jul 6 to Jul 7
NT$3,721
NT$4,102 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (654 reviews)
"We had no issues staying at this property."

Reviewed on 2025/6/13

Holiday Inn Express Middlesboro by IHG
Econo Lodge Middlesboro
Econo Lodge Middlesboro
2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is NT$2,525 per night from Jul 6 to Jul 7
NT$2,525
NT$2,784 total
Jul 6 - Jul 7
includes taxes & fees
7/10 Good! (396 reviews)
"There for a 4 day trip with friends, staff was great and the room was clean and comfy! Ive stayed here on this trip the past 5 years and its always great."

Reviewed on 2025/6/16

Econo Lodge Middlesboro
See all 319 properties in Middlesboro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Middlesboro vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Middlesboro costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Middlesboro?
If you'd like to snag a cheap Middlesboro vacation package, consider traveling in January, February and November. You'll usually find better rates on airfares and hotels during these months --- ideal for travelers wishing to save money.
How many days is enough for Middlesboro?
Generally, a handful of days is enough to explore the top attractions during your Middlesboro vacation. However, if you want to have some time to rest or take day tours, think about extending your trip.
How to find the best Middlesboro package deals?
Use Expedia's handy filters to help you find some of the best Middlesboro package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Middlesboro package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Middlesboro vacation as a package?
You can enjoy significant savings on your Middlesboro break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Middlesboro?
If you're planning an impromptu Middlesboro trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Middlesboro?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Middlesboro.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Middlesboro.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Middlesboro. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Middlesboro vacation package.

Discover the most popular places to visit in Middlesboro

Bell County Historical Society Museum

4/5(2 reviews)

You can spend an afternoon exploring the galleries in Bell County Historical Society Museum during your travels in Middlesboro. Discover the mountain views while you're in the area.

Bell County Historical Society Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.